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You could get retries working by supplying a custom HTTP client to WireMock on startup (which might just be a retry wrapper around the default client). Otherwise yes, this would be new a feature request.

We are running the wiremock docker image in kubernetes so supplying a custom HTTP client is not an option for us. I will see if I can make a contribution to the code. Thanks for your reply.

You could package your client in a JAR file then drop this in the extensions directory the WireMock Docker image adds to the classpath. Provided you’ve put the service loader file in the extension JAR WireMock will scan and automatically load your client impl.